(R)- and (S)-N-(Benzyloxycarbonyl)-3,4-epoxybutylamine. New 4-amino-2-hydroxybutyl synthons for the synthesis of hypusine reagents and (R)-6- and (S)-7-hydroxyspermidine |
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| Affiliation: | 1. Department of Chemistry and Polymer Science, Stellenbosch University, Private Bag X1, Matieland, 7602, South Africa;2. Department of Pharmacology, University of Cape Town, Private Bag X2, Rondebosch, Cape Town 7700, South Africa;3. Department of Chemistry, Emory University, Atlanta, GA, USA;1. LCC, CNRS UPR 8241, Université de Toulouse, UPS, INPT, 205 route de Narbonne, 31077, Toulouse, Cedex 4, France;2. Chemistry Department, 2036 Main Mall, UBC, Vancouver, BC, V6T 1Z1, Canada;3. ITAV, CNRS USR 3505, Université de Toulouse, UPS, 1 place Pierre Potier, 31106, Toulouse, Cedex 1, France;1. Université de Tunis EL Manar, Faculté des Sciences, Laboratoire de Chimie Organique Structurale Campus Universitaire, 2092 Tunis, Tunisia;2. Institute for Research and Physicochemical Analysis (INRAP), Pôle Technologique, Sidi Thabet, Tunisia;3. Institut Parisien de Chimie Moléculaire (IPCM), UMR 8232 Sorbonne Universités, UPMC Univ Paris 06, CNRS 4 place Jussieu, 75005 Paris, France |
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| Abstract: | The synthesis and application of the chiral reagents (R)- and (S)-N-(benzyloxycarbonyl)-3,4-epoxybutylamine is described for the first time. These 4-amino-2-hydroxybutyl synthons are successfully employed in the assembly of two hydroxylated triamines, (R)-6- and (S)-7-hydroxyspermidine, and a previously described hypusine reagent, (2S,9R)-11-[(benzyloxycarbonyl)amino]-7-(benzyloxycarbonyl)-2-[(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)-7-azaundecanoic acid, useful for solution- and solid-phase peptide synthesis. |
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